174782-10-6Relevant articles and documents
Phosphonoamidates & Phosphopnoamidines: A convenient Synthesis, Spectroscopic Properties, DFT Calculations & Pharmacological Studies
Akacha, Azaiez Ben,Ali, Ridha Ben,Arfaoui, Youssef,Hmani, Hedia,May, Michèle Véronique El,Omrani, Rania,Raddaoui, Anis
, (2021)
A series of phosphonoamidates and phosphonoamidines derivatives have been prepared with high yields and their conformations were determined. All compounds were characterized by IR, NMR Spectroscopy (1H, 13C, and 31P) and in some cases by elemental analysis and evolution study by 31P-NMR in an external lock with D2O. A DFT calculations studies was performed to identify the stability of all forms (Cis and Trans) (Syn and Anti) at the B3LYP/6-311G** level. The most stable geometry with an Anti-conformation. A comparison with the experimental results validates the level of theory. The biological activity of dimethyl cyclohexyl carbamoylphosphonate (MAmP) and diethyl cyclohexyl carbamoylphosphonate (EAmP) was evaluated. Only the association of ethyl group with phosphorus in amide gives antimicrobial capacity against S. aureus. The evaluation of the analgesic activity following a thermal stimulus showed that the rats treated with the MAmP do not present any sensation of pain. The MAmP molecule had a dose-dependent significant analgesic activity comparable to morphine effect. The hot plate test showed that the EAmP had a significant analgesic effect less than morphine and MAmP. The new compounds at low dose treatment cause an increase in the sensation of pain following a chemical stimulation that induces inflammation. So the EAmP and the MAmP can be morphemic molecules. The morphine mediates a proinflammatory phenotype and induces hyperalgesia. The MAmP was characterized by analgesic activity comparable to morphine and the EAmP was characterized by specific antimicrobial activity against S. aureus.
A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates
Kaboudin, Babak,Zahedi, Hazegh
experimental part, p. 250 - 253 (2010/01/18)
A simple, efficient, and general method has been developed for the synthesis of carbamoyl and thiocarbamoyl phosphonic esters using CaCl 2 as an efficient Lewis base catalyst. Carbamoyl and thiocarbamoyl phosphonic esters were obtained in good
Carbamoylphosphonates, a new class of in vivo active matrix metalloproteinase inhibitors. 1. Alkyl- and cycloalkylcarbamoylphosphonic acids
Breuer, Eli,Salomon, Claudio J.,Katz, Yiffat,Chen, Weibin,Lu, Shuiming,R?schenthaler, Gerd-Volker,Hadar, Rivka,Reich, Reuven
, p. 2826 - 2832 (2007/10/03)
Matrix metalloproteinases (MMPs) are a family of over 20 zinc-dependent enzymes that hydrolyze connective tissue and are involved in a variety of diseases, which are associated with undesired tissue breakdown. This paper reports the synthesis, characteriz